Hydrochloric Acid → (E)-4-(3-(3,5-dichlorophenyl)-4,4,4-trifluorobut-1-enyl)-2-methylbenzoic acid

HRID 1503666Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([C:24]([F:27])([F:26])[F:25])/[CH:10]=[CH:11]/[C:12]2[CH:22]=[CH:21][C:15]([C:16]([O:18]CC)=[O:17])=[C:14]([CH3:23])[CH:13]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.Cl>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([C:24]([F:27])([F:25])[F:26])/[CH:10]=[CH:11]/[C:12]2[CH:22]=[CH:21][C:15]([C:16]([OH:18])=[O:17])=[C:14]([CH3:23])[CH:13]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a stirred solution of (E)-ethyl 4-(3-(3,5-dichlorophenyl)-4,4,4-trifluorobut-1-enyl)-2-methylbenzoate (1.7 g, 4.0 mmol) in 1,4-dioxane (10 mL) was added 11 N HCl (30 mL), and the reaction mixture was heated at 100° C. for 48 h. The reaction mixture was cooled to 25° C. and concentrated under reduced pressure. The residue was diluted with H2O and extracted with chloroform (CHCl3). The combined organic layer was dried over Na2SO4 and concentrated under reduced pressure, and the crude compound was washed with n-hexane to afford the title compound as a white solid (0.7 g, 50%): mp 142-143° C.; 1H NMR (400 MHz, DMSO-d6) δ 12.62 (br s, 1H), 7.81 (d, J=8.0 Hz, 1H), 7.66 (s, 3H), 7.52-7.44 (m, 2H), 6.89 (dd, J=16.0, 8.0 Hz, 1H), 6.78-6.74 (d, J=16.0 Hz, 1H), 4.84 (m, 1H), 2.50 (s, 3H); ESIMS m/z 387.05 ([M−H]−); IR (thin film) 3448, 1701, 1109, 777 cm−1.

Workup

temperatureThe reaction mixture was cooled to 25° C.
concentrationconcentrated under reduced pressure
additionThe residue was diluted with H2O
extractionextracted with chloroform (CHCl3)
dry with materialThe combined organic layer was dried over Na2SO4
concentrationconcentrated under reduced pressure
washthe crude compound was washed with n-hexane

Sources & evidence

ORD record: ord-5f88046a16d54e178981b13ea6551cfa
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09212164B2

Reaction notes

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